(4-Nitrophenyl)acetic acid → 2-(4-nitrophenyl)-1-phenylethanone

Temperature

0 °C

To a solution of 4-nitrophenylacetic acid (200 g) in benzene (1.5 L) was added oxalyl chloride (200 mL). The mixture was warmed to 50°-60° C. for 2 hrs, after which time benzene and excess oxalyl chloride were distilled off under vacuum at 50° C. until a final volume of 500 mL was achieved. The residue was diluted with benzene (1 L) and cooled to 0° C. To this was added anhydrous aluminum chloride (160 g) portion-wise over 15 minutes. Thereafter, the mixture was stirred overnight at room temperature. The reaction mixture was poured over a mixture of ice (3 L) and concentrated HCl (1 L). The resulting slurry was filtered through celite and the precipitate washed with ethyl acetate. The combined filtrates were washed with water, saturated sodium bicarbonate and with brine, dried over sodium sulfate and evaporated to give 227 grams of 2-(4-nitrophenyl)-1-phenylethanone.

1. temperatureThe mixture was warmed to 50°-60° C. for 2 hrs
2. distillationafter which time benzene and excess oxalyl chloride were distilled off under vacuum at 50° C. until a final volume of 500 mL
3. additionThe residue was diluted with benzene (1 L)
4. additionTo this was added anhydrous aluminum chloride (160 g) portion-wise over 15 minutes
5. additionThe reaction mixture was poured over a mixture of ice (3 L) and concentrated HCl (1 L)
6. filtrationThe resulting slurry was filtered through celite
7. washthe precipitate washed with ethyl acetate
8. washThe combined filtrates were washed with water, saturated sodium bicarbonate and with brine
9. dry with materialdried over sodium sulfate
10. customevaporated

ORD record

ord-de046a3dc61842c9974c8cf285dfda5e

Source dataset

uspto-grants-1992_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05149709